Clomifene

Base Information

• Chemical Name: Clomifene
• CAS No.: 15690-55-8
• Molecular Formula: C₂₆H₂₈ClNO
• Molecular Weight: 405.967
• Hs Code.: 2922299090
• European Community (EC) Number: 213-008-6
• UNII: 3JU1DU3652
• DSSTox Substance ID: DTXSID601317947
• Nikkaji Number: J7.163C,J9.660A,J9.012C
• Wikipedia: Clomifene,Zuclomifene
• Wikidata: Q27257344
• NCI Thesaurus Code: C66870
• RXCUI: 2596
• Pharos Ligand ID: JCJU3BZRM8FS
• Metabolomics Workbench ID: 124125
• ChEMBL ID: CHEMBL167779
• Mol file: 15690-55-8.mol

Synonyms:Chloramiphene;Citrate, Clomiphene;Clomid;Clomide;Clomifen;Clomifene;Clomiphene;Clomiphene Citrate;Clomiphene Hydrochloride;Clostilbegit;Dyneric;Gravosan;Hydrochloride, Clomiphene;Klostilbegit;Serophene

Chemical Property of Clomifene

Chemical Property:

• Melting Point: 156.5-158.0°
• Boiling Point: 509°Cat760mmHg
• PKA: 9.60±0.25(Predicted)
• Flash Point: 261.6°C
• PSA: 12.47000
• Density: 1.104g/cm³
• LogP: 7.36460
• XLogP3: 7.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 9
• Exact Mass: 405.1859422
• Heavy Atom Count: 29
• Complexity: 481

Purity/Quality:

99%, ^*data from raw suppliers

CIS-CLOMIPHENE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Infertility Agents
• Canonical SMILES: CCN(CC)CCOC1=CC=C(C=C1)C(=C(C2=CC=CC=C2)Cl)C3=CC=CC=C3
• Isomeric SMILES: CCN(CC)CCOC1=CC=C(C=C1)/C(=C(/C2=CC=CC=C2)\Cl)/C3=CC=CC=C3
• Recent ClinicalTrials: Use of Clomiphene Citrate as an Inhibitor of Ovulation in an Oocyte Cryopreservation Cycle
• Recent EU Clinical Trials: Letrozole or Clomifene, with or without metformin, for ovulation induction in women with polycystic ovary syndrome: a 2x2 factorial design randomised trial (The LOCI trial)

Technology Process of Clomifene

There total 40 articles about Clomifene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

zuclomiphene binaphthyl hydrogen phosphate → Zuclomiphene (911-45-5,15690-55-8,15690-57-0)

Guidance literature:

With potassium carbonate; In water; ethyl acetate; at 20 ℃; for 5h;

Reference yield: 55.0%

cis-1-Chloro-2-(4-hydroxyphenyl)-1,2-diphenylethylene (72474-40-9) + 2-chloro-N,N-diethylethylamine hydrochloride (869-24-9) → Zuclomiphene (911-45-5,15690-55-8,15690-57-0)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 70 ℃;

Reference yield:

1-Bromo-2-phenylacetylene (932-87-6) → clomiphene (911-45-5,15690-55-8,15690-57-0) + Zuclomiphene (911-45-5,15690-55-8,15690-57-0)

Guidance literature:

Multi-step reaction with 5 steps

1: N-iodo-succinimide; N-chloro-succinimide / 1,2-dichloro-ethane / 24 h / 30 °C / Sealed tube

2: palladium diacetate; tricyclohexylphosphine; potassium hydroxide / tetrahydrofuran; water / 2 h / 80 °C / Inert atmosphere

3: potassium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran; methanol / 12 h / 110 °C / Schlenk technique

4: boron tribromide / dichloromethane / 25 h / -78 - -20 °C

5: potassium carbonate / acetone / 1 h / 60 °C

With N-chloro-succinimide; N-iodo-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium diacetate; boron tribromide; potassium carbonate; potassium hydroxide; tricyclohexylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; acetone;

DOI:10.1002/cjoc.202100472

upstream raw materials:

N,N-diethyl-2-[4-(1,2-diphenylvinyl)phenoxy]ethylamine hydrochloride

4-<2-(diethylamino)ethoxy>iodobenzene

(E)-bis(trimethylstannyl)stilbene

p-Iodophenol

Downstream raw materials:

(Z)-1-<4-(2-diethylaminoethoxy)phenyl>-1,2-diphenyl-1-penten-5-ol

cis-clomiphene citrate

clomiphene citrate

Refernces

• 1、 -. "Processes for the Preparation of Zuclomiphene and Intermediates Thereof". Paragraph 0147-0149. . Retrieved 2021/05/21.
• 2、 Blazecka, Peter,Chung, Andrew,Emmett, Michael,Green, Stuart,Karadeolian, Avedis,Le Sueur, Richard,Patel, Dineshkumar,Rey, Allan,Souza, Fabio,Zhao, Yajun. "Stereoselective Nickel(II)-Catalyzed Addition of Aryl Grignards to Diphenylacetylene in the Synthesis of Zuclomiphene". . . Retrieved 2022/03/16.